Optically active β-hydroxy-α-aminocarboxylic acid derivatives are important intermediates for compounds useful as several fine chemical materials represented by physiologically active substances such as pharmaceuticals and agrochemicals, etc.
As a process for producing optically active β-hydroxy-α-aminocarboxylic acid derivative, a process is known in which a racemic α-aminoacyl acetic acid ester compound is subjected to asymmetric hydrogenation by catalytic asymmetric hydrogenation with ruthenium-optically active phosphine complex catalyst to produce syn-selectively an optically active β-hydroxy-α-aminocarboxylic acid derivative (see, for example, Non-patent Documents 1 and 2, and Patent Document 1).On the other hand, asymmetric hydrogenation with a transition metal catalyst of olefins, ketones and imines has been known well (see, for example, Non-patent Document 3).In addition, it is reported an anti-selective process for producing 3-(3,4-dihydroxyphenyl) serine derivative being one of β-hydroxy-α-aminocarboxylic acid derivatives by asymmetric hydrogenation with a rhodium catalyst containing (+)-DIOP as an asymmetric ligand (see, for example Patent Document 2).Further, an example of asymmetric hydrogenation with a rhodium complex containing a specific ferrocene derivative as a ligand is known (see, for example Patent Document 3).However, hydrogenation in the presence of an acetic acid salt has not been known.Patent Document 1: JP-A-6-80617 (1994)Patent Document 2: JP-A-2-172956 (1990)Patent Document 3: EP-A-0612758 (1994)Non-patent Document 1: J. Am. Chem. Soc., 1989, 111, p. 9134-9135Non-patent Document 2: SYNTHESIS, 1992, p. 1248-1254Non-patent Document 3: R. Noyori ed. Asymmetric Catalysis in Organic Synthesis, (1994) Jhon Wiley & Sons, Inc, New York